> This is an example of bad technology failing its user.

I don't think that's fair to say. You can literally import PDF files in Word via the most common File > Open dialog. [1] You can also save as PDF in Word via the File > Save As dialog. [2] These are not exactly some obscure hidden functions.

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[1] https://support.office.com/en-us/article/edit-pdf-content-in...

[2] https://support.office.com/en-us/article/save-or-convert-to-...

You can also right click a pdf > Open with > Word.

But the default does not protect users. Putting the onus on users to protect themselves is the problem.

Actually that's one example where lack of privacy accidentally leads to a good outcome for society.

Also he was not failed by a piece of software. They recovered the document from his email. How would his email strip the document of identifying information?